Benzoyl chloride, 3-bromo- → 3-Bromo-N-(3-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yloxy)phenyl)benzamide
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[NH:12][C:13](=[O:15])[NH:14][C:7]=12.[Br:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23](Cl)=[O:24]>>[Br:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23]([NH:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:4]([O:5][C:6]2[CH:11]=[CH:10][N:9]=[C:8]3[NH:12][C:13](=[O:15])[NH:14][C:7]=23)[CH:3]=1)=[O:24]Participants
Procedure
Method H was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and 3-bromo-benzoyl chloride to afford the title compound as a light brown solid (50 mg, 73%). 1H-NMR (δ, ppm, DMSO-d6): 6.50 (d, 1H, HPy,5, J=6.0 Hz), 6.92 (d, 1H, Harom, J=8.0 Hz), 7.43 (ps t, 1H, Harom, J=8.0 Hz), 7.48 (m, 1H, Harom), 7.62 (s, 1H, Harom), 7.66 (d, 1H, Harom, J=8.0 Hz), 7.78-7.84 (m, 2H, Harom+Py,6), 7.93 (d, 1H, Harom, J=8.0 Hz), 8.12 (s, 1H, Harom), 10.45 (s, 1H, NHamide), 11.23 (s, 1H, NHPy3), 11.44 (s, 1H, NHPy2). 13C-NMR (δ, ppm, DMSO-d6): 106.58, 110.82, 113.83, 114.62, 116.32, 121.66, 126.87, 128.24, 130.65, 130.87, 131.71, 136.80, 140.56, 141.08, 144.67, 147.00, 154.17, 154.68, 164.13. HRMS (EI): m/z [M+H] calcd for C19H14BrN4O3: 425.0249; found: 425.0248.
Sources & evidence
- ORD record
- ord-626844d69389449da4f777d920bf861a
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07951819B2
Reaction notes
Loading…